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Stokes was born in Shelby County, Tennessee, in the vicinity of Whitehaven, located two miles north of the Mississippi state line.[3] There is uncertainty over his year of birth; his daughter and later sources reported 1888, but the researchers Bob Eagle and Eric LeBlanc give 1877, the date on his World War I draft card.[1]

In the mid-1910s, Stokes joined another Mississippi musician, Garfield Akers, as a blackface songster, comedian, and buck dancer in the Doc Watts Medicine Show, a tent show that toured the South. During this period of touring, Stokes developed a professionalism that set him apart from many of the more rural, less polished blues musicians of that time and place. It is said that his performances on the southern minstrel and vaudeville circuit around this time influenced the country singer Jimmie Rodgers, who played the same circuit. Rodgers borrowed songs and song fragments from Stokes and was influenced stylistically as well.[6]

Around 1920, Stokes settled in Oakville, Tennessee, where he went back to work as a blacksmith.[3] He teamed up again with Sane, playing dances, picnics, fish fries, saloons, and parties in his free time. The two joined Jack Kelly's Jug Busters to play at white country clubs, parties, and dances. Stokes and Sane performed on Beale Street as the Beale Street Sheiks and first recorded under that name for Paramount Records in August 1927.[3] Stokes eventually cut 38 sides for Paramount and Victor Records. "The fluid guitar interplay between Stokes and Sane, combined with a propulsive beat, witty lyrics, and Stokes's stentorian voice, make their recordings irresistible."[7] Their duet style influenced the young Memphis Minnie in duets with her husband, Kansas Joe McCoy.[5]

The Sheiks next recorded at a session for Victor Records in February 1928, at which Furry Lewis also recorded.[5] At this session, the emphasis was on blues rather than the older songs that were also part of Stokes's repertoire. Stokes recorded again for Victor that August, playing "I Got Mine", one of a body of pre-blues songs about gambling, stealing and living high. He also recorded the more modern "Nehi Mama" (or "Nehi Mama Blues", also rendered as "Nehi Mamma Blues"), the title being a pun on the name of the Nehi soft drink and the knee-high skirts that were fashionable at the time. Sane joined Stokes for the second day of the August 1928 session, and they produced a two-part version of "Tain't Nobody's Business if I Do", a song well known in later versions by Bessie Smith and Jimmy Witherspoon but whose origin lies in the pre-blues era.[8] The Sheiks also continued to busk on the streets and perform at parties.[5]

In 1929, Stokes and Sane recorded again for Paramount, resuming their billing as the Beale Street Sheiks for a few cuts. In September, Stokes was back with Victor to make what were to be his last recordings, this time without Sane but with Will Batts playing the fiddle.[3] Stokes and Batts were a team, as evidenced by these records, which are both traditional and wildly original, but their style had fallen out of favor with the record-buying public. Stokes was still a popular live performer, however, appearing in medicine shows, the Ringling Brothers Circus, and other tent shows and similar venues during the 1930s and 1940s. In the 1940s, he moved to Clarksdale, Mississippi, and occasionally worked with Bukka White in local juke joints.[3]